[webstersII]

“The problem with encryption is so few people use it that it it’s almost certainly a red flag for multiple agencies.”

How would they even know it’s encrypted?

Isn’t it just an attachment you send?

[expat1000]

I guess you could send it as an attachment, but PGP is typically right in the body of the message.
This whole thread is about gmail and Yahoo reading your email - of course they would know - even without the -PGP- header it inserts. But as an attachment, possibly zipped and password protected - I am not sure.